Disazo-dyestuffs insoluble in water



wherein R represents a methyl or ethyl group.

United States PatentO Ho 139,146

Patented Mar. 20, 1956 greenish to reddish hue having a high coloringstrength, 2,139,146 v good fastness to solvents and a very good fastnessto DISAZODYESTUFFS INSOLUBLE IN WATER light. They are, therefore,especially suitable for coloring plastics, .pr'inting ink and forspecial applications in Reinhold Weigele and Richard Huss, Frankfurt amMain, the lacquer, wallpaper and paper industries.

Germany, assignors to Farbwerke Hoechst Aktieng I As compared with thedyestuff from tetrazotized 4.4- gesellschaft yormals Muster Lucms & z.stamina-cs3 --dichlorodiphenyl and acetoacetylaminofurt am Mam, Germany,a company of Germany benzene described in U. S. Patents Nos. 2,410,219and N Drawing Applicatiolnecember4 1953, 2,478,767 as well as thedyestutf obtainable'by coupling serial 95,347 10 tetrazotized4.4-diamino-3.3-dimethoxydiphenyl with 1- acetoace'tylamino -.2.5dimethoxy 4 cyanobenzene de- Clalms Prionty apphcatmn Germany Decembers'1952 scribed in German Patent No. 842,819, the new dyestufis 2 c 2 0.11' are distinguished by a substantially improved fastness to light. Thepresent invention relates to disazo-dyestuifs in- 15 The following f pServe f illustrate the invensoluble in water; more particularly, itrelates to dyestufis tion, but 1t 15 110i Intended to It thereto, theParts of the general formula being by weight unless otherwise stated,and the rela- H10 CH:

in which R represents a methyl or ethyl group. tionship of parts byweight to parts by volume being the In our co-pending U. S. applicationSerial No. 320,102, same as that of the kilogram to the liter:

filed November 12, 1952, there is described a process for producingwater-insoluble disazo-dyestufis by coupling in I substance or on asubstratum suitable for the production h of 'dlehlerodlphenyl are oflakes the tetrazo compound of 4.4'-diamino-3.3-disurfed Wlth 600 Partsby Volume of Water and P i chlorodiphenyl with anacetoacetylaminobenzene of the 5 by Volume 5 N'hydroehlene heldh mlxture15 general f mula then cooled w1th we to 0 C., and tetrazotized at 0 C.

with 52.5 parts by volume of a solution of sodium nitrite of 40 percent. strength. The clarified tetrazo-solution is run, while stirringwell, at 30 C.-33 C. into an acetic CHsCO-CHaGO'-NH 4o acid suspensionof 115 parts of 1-acetoacetylamino-4- R chloro-2.5-dimethoxybenzene ofthe formula Example wherein R represents an alkyl or aryl radical.

The disazo-dyestufrs so obtained are water-insoluble pigments of aclear, yellow color which, owing to their coloring strength, their goodfastness to solvents, light CH and transparency are especially suitablefor coloring plastics, printing ink and for special applications i h thepH value of the coupllng medium bemg maintained at lacquer, wallpaperand paper industries, 5.5-4.5. When the fOlIl'lQtlOIhOf the dyestufi 1scom- We have found that water-insoluble disazo-dyestufis Pieter themlxhhe bohed Wlth stem: the dyeswfi 13 having the same good fastnessproperties and similar tints then Separated 111 h usual e washed. hhhlhehh'al are obtained by coupling in substance, or on a substratum and fThe Plgmeht h h e eehshthtes e suitable for the production of lakes, thetetrazo-come Yehew PeWder whleh 1s hshhghlshed by a hlgh pound f diaminodichlowdiphenyl with an coloring strength and transparency as well as avery good acetoacetylaminobenzene of the following general forfasthessto h mula I The coupling can be carried out with advantage m thepresence of a resin soap.

OR By using in the above example 126 parts ofl-acetoacetylamino-4-chloro-2.S-diethoxybenzene instead of 115 parts of1-acetoacetylamino-4-chloro-2.5-dimethoxyben- 6o zene, a somewhat moregreenish yellow powder of simi- R lar fastness properties is obtained.

We claim:

1. The water-insoluble disazo-dyestuffs corresponding to the generalformula:

CHI-C O-GHr-C O-NH C1 The new dyestuffs are clear yellow pigments of a V2,789,146 I V 3 I 4 wherein R represents a member of the groupconsisting of 2. The water-insoluble disazo-dyestufi correspondingmethyl and ethyl. to the following formula References Cited in the fileof this patent UNITED STATES PATENTS 1,933,431 Henle et a1. Oct. 31,1933 2,410,219 Langstroth Oct. 29, 1946 2,453,692 von Glahn' Nov. 16,.1948 2,478,767 Locke Aug. 9, 1949 2,657,204 De Lucia et a1 Oct. 27,1953

1. THE WATER-INSOLUBLE DISAZO-DYESTUFFS CORRESPONDING TO THE GENERALFORMULA: